1. Field of the Invention
This invention relates to uridine analogs and, in particular, to making and using nucleoside phosphates having a 5-aminouracil group.
2. Description of the Related Art
Uracil is a nucleic acid base, that, when bound to ribose or deoxyribose, forms uridine or deoxyuridine, respectively. Certain analogs of uridine and deoxyuridine have been prepared and used in different applications.
For example, deoxyribouridine analogs containing a 5-amino group have been prepared and used as anticancer, antiviral, or antibacterial agents. Such uses may be found, for example, in Shepard, Patent No. WO 2001/007088; Shepard, Patent No. WO 2001/007087; Shepard, et al., Patent No. WO 99/37753; Shepard, Patent No. WO 99/08110; Wigerinck, et al., J. Med. Chem., 34:1767–1772 (1991); Cinatl, et al., Chemotherapy, 37:128–133 (1991); Beck, et al., Adv. Ext. Med. Biol., 195B:97–104 (1996); Desgranges, et al., Biochem. Pharmacol., 32:3583–3590 (1983); Balzarini, et al., Biochem. Pharmacol., 31:3673–3682 (1982); Hampton, et al., J. Med. Chem., 25:644–649 (1982); Balzarini, et al., Proc. Int. Roundtable Nucleosides, Nucleotides Biol. Appl. 4:275–291 (1982); Hampton, et al., J. Med. Chem., 22:1524–1528 (1979); Hampton, et al., J. Med. Chem., 22:621–631 (1979); Lee, et al., Biochemistry, 15:3686–3690 (1976); Leung, et al., Biochem. Med., 16:127–137 (1976); Cheng, et al., Biochemistry, 13:1179–1185 (1974); or Roy-Burman, et al., Biochem. Pharmacol. 19:2745–2756 (1970). Other nucleotide analogs have been described in, for example, Verdine, et al., Patent No. WO 98/00433; Hayashibara, et al., J. Am. Chem. Soc., 113:5104–5106 (1991); Hayashibara, et al., Biochemistry, 31:11265–11273 (1992); or Mascareñas, et al., J. Am. Chem. Soc., 115:373–374 (1993).
Other 5-amino deoxyribouridine analogs have been synthesized and analyzed, for example, in Ferrer, et al., Bioconjugate Chem., 8:757–761 (1997); Ferrer, et al., Nucleosides Nucleotides, 15:907–921 (1996); Barawkar, et al., Bioorg. Med. Chem. Lett., 3:347–352 (1993); Eriksson, et al., Biochem. Biophys. Res. Commun., 176:586–592 (1991); Baerwolff, German Patent No. DD 137110; or Tetrahedron, 48:8505–8514 (1992). In some cases, 5-amino deoxyribouridine analogs have been derivitized with fluorescent compounds, for example, in Jadhav, et al., Nucleosides Nucleotides, 16:107–114 (1997). 5-amino deoxyribouridine analogs have also been prepared for DNA sequence determination, such as in Dyatkina, et al., Nucleic Acids Symp. Ser., 18:117–120 (1987).